The transformation of epicandicandiol into a gibberellin A12 isomer

Add time:08/21/2019    Source:sciencedirect.com

Favorskii rearrangement of a chloro-enol-lactone (7), obtained in two steps from the diterpene epicandicandiol (1), afforded 9, which after hydrolysis led to the gibberellin A12 isomer 10 The stereochemistry of the affected centres has been established as 5α-H, 6β-H revising the previously assigned 5β-H, 6α-H. The structures of minor products obtained in the autoxidation of 7-oxo-ent-kaur-16-en-18-methyl ester and in the reduction of 7-oxo-ent-kaur-5,16-dien-18→6-olide have also been established.

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